


Milestones

by aly_m_cap



Series: Milestone [1]
Category: Supernatural, Supernatural RPF
Genre: F/M, Fluff
Language: English
Status: In-Progress
Published: 2019-03-08
Updated: 2019-06-03
Packaged: 2019-11-13 18:58:41
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,387
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18037004
Author URL: https://archiveofourown.org/users/aly_m_cap/pseuds/aly_m_cap
Summary: Your first date with Jensen Ackles went better than you could have ever hoped, leading to a long life with your favorite actor.





	1. First Date

You sat in your car, blasting the air conditioning as you tried to combat the nervous sweat that pooled in your armpits. You unlocked your phone and opened up Bumble, nervously tapping to your messages. He hadn’t messaged you, cancelling the date. Yet. 

You rummaged through your purse for deodorant. You cursed at your nerves as you applied another thick layer. You threw it back in your purse as your phone chimed. You looked at your lock screen. Bumble: Jensen sent you a new message. 

You tapped on the notification with butterflies in your stomach and unlocked your phone. Your messages seemed to take an eternity to load as you awaited the usual ‘Sorry, something came up’ message you’ve received so many times before. 

You beamed as you read his message. I’m here and got us a table in the back. 

You let out a long breath to calm your nerves before you turned your car off. You grabbed your purse and strode towards the restaurant with a newfound confidence. The hostess opened the door for you as she chirped, “Welcome to Sorge’s! How many seats will you need for tonight?” 

You shyly smiled, “I’m actually meeting someone who’s already here.” You paused to clear your throat as your nerves tried bubbling up again, “His name is Jensen. Jensen Ackles.” 

The hostess’ eyes went wide as she plastered a fake smile on her face, “Okay! Let me take you to him.” 

You nodded as you gripped your purse strap tighter and followed her through the restaurant. Your jaw dropped as the waitress walked through a separate room in the back. You expected to be shoved in a back corner of the restaurant, not a separate room with a couple tables. 

Jensen looked up from his phone when he heard the door open, shoving it in his suit jacket pocket as he stood with a smile. The hostess excused herself as Jensen walked towards you with open arms, “Y/N!” He enveloped you with his long, muscular arms, “You look amazing.” 

You giggled as he pulled away and smoothed down your dress. “Thank you.” You looked him over: white tennis shoes, dark washed jeans, gray polo and a black suit jacket. “You look,” you trailed off as you eyed him once more, “more than amazing.” 

He chuckled as he ushered you to sit down, “There’s no way I look better than you.” He pulled out your chair and pushed it in as you sat. He sat across from you and leaned forward, inching himself closer to you, “How has your day been?” 

As you got lost in the emerald of his eyes, you thought ‘better now.’ But Jensen’s laugh made you realize you had said it aloud, causing you to blush brightly with humiliation. 

“Well, I’m glad. Mine got better as I saw you walk through that door.” Your blush became deeper from his adulation, causing you to giggle. He rested his chin on a hand as he watched you with a large smile, “I like your laugh. It’s cute.” 

You put your hands over your face, trying to hide the crimson that now adorned your cheeks. Jensen snickered at your reaction as a waitress walked into the room. 

“Can I get you guys some drinks?” 

You smiled towards her, “Can I get water with lemon?” 

She nodded as she scribbled onto her notepad, “Of course!” She turned towards Jensen, “And you Mr. Ackles?” 

“I’ll actually have the same.” The waitress nodded as she turned on her heel and walked out of the small dining room.

“So, tell me something that's not on your profile” Jensen asked, looking at you quizzically. 

You were once again lost in his insanely green eyes and almost didn't hear him. You snapped back to reality and cleared your throat, “Hmm, what?” 

Jensen grinned, “Tell me something about yourself. Something that’s not online.” 

You blushed, yet again, as you tucked a stray strand of hair behind your ear. “Oh, sorry.” You paused briefly, trying to come up with some unknown factoid of yourself. “Well, I'm kind of a singer,” you said slowly. It sounded so absurd saying it out loud. Telling Jensen Ackles that you sang was like telling Joe Montana you play football. You felt like such an amateur. 

Jensen lit up, “Oh really? What's your favorite genre to sing?” 

You were almost surprised he was actually interested. You figured he would laugh it off like you were another crazed fan, but you also forgot who you were talking to for a second. Jensen would never be the type to demean someone, he's only ever supported others, especially those in the Supernatural Family. 

“I sing a little bit of everything, but mostly blues and rock. Tennessee Whiskey is one of my all time favorites.” His tongue was peeking out between his teeth as his eyes lit up at your answer.

“Tennessee Whiskey, huh? I’ve sung that a couple times with Louden Swain. It’s one of my favorites.” He paused as the waitress came in with your drinks and took your orders. “Um,” he took a sip of water and wiped at his mouth quickly, “my all time favorite song to sing though is Simple Man.” 

You smiled and looked down at your water. “I'm sorry but I have to gush…” You looked back up at him, afraid to annoy him. He was still smiling at you, so you continued. “Your cover of The Weight you all did on Jason's album was incredible”. Deep rose once again flooded your cheeks as you went back to staring at your water. You weren't sure if you crossed the line, seeming more like a fan looking for five minutes of fame than someone on a date looking for a meaningful relationship. 

He gently placed his hand on your wrist, breaking your attention for your water and back on him. “I’m glad you liked that.” He chuckled as his thumb ran over your skin lightly, sending electricity through you. “You know, you don’t have to hide the fact that you’re a fan. I knew that already and it hasn't deterred me yet.” 

You bit your lip, “I just don’t want to cross a line or anything.” 

Jensen shook his head. “You aren’t crossing a line. We’re two people, on a date, looking for forever. It’s just,” he shrugged, “one of us happens to be famous,” he smirked. 

You gave him a warm smile and relief rushed through you. 

The rest of the night, you and Jensen talked about everything under the sun. In the short period of time you had been with him, you felt more comfortable with him than people you’d known for years. 

As the date winded to a close, Jensen walked you out to your car. He cleared his throat as you opened your driver’s side door and threw your purse into your passenger seat. “So,” you turned towards him, his hands rested in his jean pockets as he rocked back and forth slightly, “I had a great time tonight.” He looked down at his feet, “I was wondering if I could get your number though, to set up another date.” 

You giggled and walked towards him, “Now you’re the nervous one?” Jensen looked up towards you with an apologetic smile. You held out your hand, causing Jensen to shoot you a confused look. “You can’t text me to set up another date if you don’t have my number.” 

“Oh!” He fished his phone out of his suit jacket and handed it to you. 

You smiled ear to ear as you typed your name and number into his contacts. You handed his phone back to him, “There.” You turned towards your car and grabbed your purse to fish out your phone, “You can text me right now so you know I didn’t give you the wrong number.” 

For the first time during the night, Jensen was blushing as he tapped on his phone screen. Your phone chimed as Jensen put his back in his suit jacket. You opened your texts to a new message from a new number. Hey, it’s Jensen. 

You smirked as you saved his number in your phone and then texted him back. Jensen who? 

He pulled his phone out of his pocket and frowned at the message as you burst out laughing. “I’m sorry, I had to.” You wiped at a small tear that escaped from laughing, “But it’s me Jensen. I look forward to another date.” 

He beamed as he wrapped you in the second embrace of the night, “That wasn’t funny you know.” He kissed the top of your head and stepped back, “But I look forward to another date as well.”


	2. One Year Anniversary

You gripped Jensen’s hand a little tighter, “Where are we going?” You asked.

He chuckled as he kept his eyes on the road, “You’ll see.” 

You looked towards the freckled masterpiece beside you, “You seriously won’t tell me?” 

He glanced towards you with a mischievous grin, “Because I want it to be a surprise. Tonight is a big night.” 

You rolled your eyes towards him, “Oh whatever, Ackles. Tonight is a big night, being together a year is a milestone.” You sighed, “But that doesn’t mean I can’t know where we’re going. I don’t know if I’m overdressed or underdressed or what. You haven’t told me anything!” 

He squeezed your hand with a small laugh as he stopped at a stop light, “You look beautiful, sweetheart. Don’t worry about being over or under dressed. You’re dressed perfectly for me.” He picked your hand up and kissed the back of it before he started driving towards your mystery destination again. 

“Ugh!” You groaned out of frustration. You looked out your window as he chuckled at you once more. He knew you weren’t one for surprises. You always like having a plan and being prepared and tonight, it felt like he was just throwing you into a pool and hoping you could swim. 

Minutes ticked by before he pulled into the same parking lot you had a year ago before your first date. You looked over at him as he turned off the ignition. “Why didn’t you just tell me we were coming here?” 

He simply smiled as he got out of the car, walked around to your side and opened the door for you. He held out his hand for you to take as you climbed out of the car, “Shall we?” You nodded as you both walked towards the restaurant. 

As you entered, the same hostess from before greeted you both at the door. “Welcome to Sorge’s, Mr. Ackles!” She gathered menus from the hostess stand, “Your private room is all set up for you. Follow me.” 

Jensen squeezed your hand gently, “Great! Thank you.” 

You both followed the waitress back to the room where you had dined one year ago. She set the menus on the table as you both settled into your seats. You picked up a menu and looked towards Jensen with a raised brow, “Are you trying to recreate our first date?” 

He smiled as he picked up his menu, “Not really, no. This is where we started, so I figured why not make it a sort of tradition.” 

“A tradition?” 

He looked over his menu at you, “Yeah. A tradition. Every anniversary we have, we can come here. Reflect on all our memories of the year.” 

You nodded as your eyes focused back towards your menu, “That sounds perfect.” 

You both decided on what to eat and drink before the waitress came to your table. As you ordered, focusing on the waitress and not himself, Jensen pulled out a small velvet box from his pocket and set it in his lap. He scrambled to grab his menu, almost dropping the box on to the floor. “Uhh, I’ll actually have what she’s having.” 

You look toward him, puzzled, as you both handed your menus to the waitress, “You want a chicken caesar salad?” 

He smiled and shrugged, “It sounds good right now.” 

“Alright. I’ve just never seen you order a salad when we’re out to dinner.” You watched him as he fidgeted in his seat, “You okay, babe?” 

You could see him swallow hard, “Yeah, yeah. I am. I jus-I just can’t wait to do this until after dinner like I planned.” 

You raised a suspicious brow towards him, “Do what?” 

He stood from the table and pulled out the box as he kneeled. You gasped when he opened it, a ring of small diamonds were set around a large sapphire stone, “Oh my god.” 

He smiled nervously, “Sweetheart, when we met here a year ago, I knew you were the girl that I wanted to spend the rest of my life with. You took my breath away and stole my heart, even though you may have thought the date didn’t go as well as you wanted.” You both laughed softly. “You will make me the happiest man in the world if you say yes.” He paused as he swallowed thickly, “Y/N, will you marry me?” 

You nodded frantically, “Yes, Jensen! YES!” He beamed as he slid the ring on your finger. You looked at it for a couple seconds before you wrapped your arms around his neck. His arms in turn wrapped around your waist tightly as you spoke, “It’s beautiful.” 

He pulled away and gave you a deep kiss. “I’m glad you like it. It took me months to find the perfect ring.” He snickered, “I would have proposed before now if it hadn’t taken me so long to find it.” 

You giggled, “Well, tonight was just as good as any to do this.” 

As you both stepped away from each other, the door to the private room burst open with all the employees of the restaurant yelling, “Congratulations!” 

You cheeks turned crimson as Jensen waved them off, “Thank you guys.” They all smiled as they walked away from the room. When the door swung closed fully, Jensen looked towards you with adoration, “I love you, Y/N.” 

You grabbed his hands softly, “I love you too, Jensen.”


	3. Your Wedding Day

“Breathe, Y/N,” Geneveive pleaded with you as she fussed with your hair.

Abby, your best friend, piped up from behind you as she zipped your dress, “Yeah, breathe chick. Everything is going to be fine. Jensen is going to lose it when he,” you could feel her hook the top of the zipper together and then step beside you, “sees you in this.” 

You let out a nervous chuckle as you tried peaking a view in the mirror around Gen, but her short stature in heels still somehow blocked your view. “I know guys, it’s just, this is a huge step. We’ve been together for years but today makes things different.” 

Gen smiled as she left your hair alone, placing her hands on your arms to comfort you. “I know hun. I was the same way with Jare. But, Abby is right. Jensen is going to lose it when he sees you.” She stepped to your side opposite the one Abby was standing on, letting you finally see yourself in the mirror. 

You softly gasped. Was that really you? You stared at yourself, dumbfounded at how the girl in the mirror looked. Her Y/E/C eye’s emphasized to a piercing hue by eyeshadow and eyeliner. Her plump, pink lips glossed over. Her Y/E/C, longer than usual thanks to extensions, cascaded down her front in loose curls over her soft blue wedding dress. The dress clung to her curves in all the right places, accentuating all the parts of her body that Jensen loved. 

But her was you. 

You looked between Gen and Abby, “How… How did you guys do this?” 

Gen giggled, “We didn’t do anything but enhance your natural beauty.”

You rolled your eyes towards her, “Well, I would never be able to do this to myself.” You turned and hugged her, then your best friend, “Thank you guys. For everything, especially doing this,” you said as you motioned towards yourself, “since I didn’t want a whole makeup team.” 

Abby shrugged, “Even if you did, I wouldn’t have let them touch you.” 

The three of you chuckled as a knock rapped on the door. “Y’all decent? Can I come in?” 

Gen walked towards the door, still chuckling, “Come in, babe.” 

Jared stepped through the bridal suites threshold, giving Gen a quick kiss. “You look beautiful, babe.” He turned towards you, as his eyes grew wide, “Wow, Y/N. Jensen, Jensen is going to lose it.” 

You couldn’t help but giggle, “Everyone keeps saying that.” 

He came towards you, enveloping you in a strong and warm hug, “Well, we’re right.” He looked towards Abby, “Y’all look great.”

“Thanks Jared.” She glanced towards the closed door and asked, “How’s the groom?” 

Jared smiled, “Excited and nervous.” He laid a hand on your arm, “He’s ready to make you Mrs. Ackles, that’s for sure.” 

You bit at your lip, forgetting about the gloss, “I’m ready to be Mrs. Ackles.” 

Jared did a silent cheer, throwing fists into the air and causing you all to erupt into giggles. He walked towards the door, “I’ll go back to the groom so we can get things started!” 

Abby walked around you, checking over your hair and makeup one last time before she placed her hands on your arms like both Jared and Gen had in the last ten minutes. She rubbed your arms softly, “I’m so happy for you, Y/N. You finally found your prince charming.” You nodded as she started to tear up, “you deserve this, to be happy, after everything you’ve been through,” the dam broke, “That’s all I ever wanted for you hun, you deserve all the happiness in the world, and then some.” She hugged you tightly and continued to cry, only to pull back and have Gen blot her face to save some of her makeup. 

You playfully smacked her arm as you blotted at the tears that fell on your face, “You’re going to make me ruin the masterpiece you created!” 

“Don’t worry, I can fix anything that may be messed up.” She chuckled as he checked her face in the mirror, “But, there’s a reason why I used waterproof mascara.” 

Another knock came at the door, “Abby, Gen, we’re lining up now.” 

Gen hugged you softly, “You going to be okay, Y/N?” 

You nodded, “Yeah Gen, see ya in a few.” 

The girls grabbed their bouquets, leaving yours on a chair by the door, as you walked towards the mirror to look over yourself again. 

Taking a deep breath, you smoothed your hands over your dress and then walked towards the door to grab your bouquet. You cracked the door, peeking out to see if the wedding party had begun walking down the aisle yet. But, the owner of the small church walked towards your room, blocking your view. 

“Y/N. You can line up at the door now, everyone is up front.” 

You opened the door slowly before walking out into the hallway. As you stopped in front of the grand, black doors that separated you from the ceremony, the owner of the church fixed your dress behind you. You mouthed ‘thank you’ towards her before you could hear a muffled Here Comes the Bride on the other side of the door. 

The owner steps up beside you, “The doors will open on three and then you can begin walking, okay?” 

You nodded and took one final breath as she counted to three on her fingers in front of you. 

Light flooded your eyes as the doors opened slowly. As your eyes grew accustomed to the sensory overload, they darted down towards the front of the church and landed on Jensen. A large smile crept across your face as you watched your soon-to-be husband. He wrung his hands at his chest as he bit his lip in excitement. 

Your eyes never left each other as you made your way towards him. As you approached, you turned towards Abby, handing her your bouquet before she straightened out your dress. 

Turning back towards Jensen, your hands slipped into his as he stared down at you in adoration. “You look absolutely beautiful, sweetheart.” 

Before you could respond, the pastor began the ceremony. You vaguely registered what he said, saying the vows he asked you to say when prompted, but your attention was mainly focused on Jensen. The way his emerald-green eyes sparkled as he looked at you, how his hands squeezed yours periodically with excitement, and how the tip of his tongue laid across his bottom lip occasionally. 

Before you knew it, the pastor said, “You may kiss the bride.” 

Jensen’s hands cupped your cheeks softly before his lips came crashing down against yours. As he pulled away, you chuckled at the gloss stuck to his own lips before Abby patted you on the shoulder and handed you your bouquet. You nodded towards her in thanks before you and Jensen ran up the aisle. 

You both ran until you stopped in the private room you were going to be meeting with your guests before your reception. Jensen picked you up and spun you around the room, causing you to giggle, before he kissed you once more. “Y/N, my god.” He set you down, taking one hand into his before twirling you slowly, “You look, breathtaking.” 

You looked down towards your dress, “Yeah? Thank Gen and Abby, only they could do this.” 

Jensen shook his head, “No, you always look beautiful. But, now? Being Mrs. Ackles makes you even more beautiful.” 

You hit his shoulder playfully, “You’re too cheesy, Jay.” 

He chuckled as he rubbed his arm dramatically, “I know,” he pick you up again, “You love it though.” His lips connected with yours again, softer this time but with no less passion, before he set you down. “I’m never going to get tired of calling you Mrs. Y/N Ackles though.” You placed another small kiss on his lips before guests started to filter into the room. 

You both mingled for a short period of time before you were pulled away to be taken to your reception venue. 

As you both sat in the limousine, Jensen squeezed your hand, “Mrs. Y/N Ackles. Mm!” You looked towards him, a goofy smile plastered across his face, “Music to my ears.” 

You shook your head and laughed as the limousine pulled up to Jensen’s family Lake House. His mother and father had went above and beyond, decorating the trees and patio with fairy lights, setting the tables with orchids and candles, and lining a huge buffet table with food. 

You and Jensen walked into the house, hand in hand, to find Alan and Donna. 

Alan rounded the corner from the kitchen, a large plate of food in hand, before he stopped and grinned, “Hey you two!” He craned his head back towards the kitchen as he yelled, “Donna! They’re here!” 

You heard a squeal from the kitchen before Donna burst out of the door and wrapped you in a warm hug. She stepped back as she ogled over your dress, “Oh, Y/N. You were so beautiful, you are so beautiful.” She turned towards Jensen, kissing him on the cheek, “Hi honey.” She lowered her voice and stepped closer to you both, “Go out and steal some food before everyone else arrives.” 

Jensen chuckled, “Alright, mom.” He stepped away and called over his shoulder, “I’ll grab you something too, sweetheart.” 

“Okay, babe.” You turned back towards Donna, “Thank you so much, for all of this. It looks amazing outside.” 

She waved you off, “It was nothing dear. Afterall, we just want the best for you and Jense.”

“We appreciate your hospitality and offering to put all this on for us,” you said blushing slightly. “I wish my parents were here to help you out but..-“ 

She cut you off, “Don’t worry about it, Y/N. You’re family now. We take care of family.” 

Jensen rushed back in with a plate and a half full of food, “People are starting to pull up outside, we gotta hide, sweetheart.” 

You both walked to the back of the house, sneaking into the master bedroom, before guests saw you. You both grazed slowly as you waited for the guests to filter in and be seated. When you both heard music begin to play and the DJ talk into the mic, announcing the wedding party, you both stopped eating and made your way slowly out the door. 

“And, finally. The moment you’ve all been waiting for,” the DJ peered into the house, waiting for a go ahead from Donna. She rushed towards you both, lightly pushing you towards the door as the DJ announced, “Mr. and Mrs. Jensen Ackles!” 

Jensen took your hand before you both walked out onto the patio, raising your hands above your heads as he cheered, “Yeah!” 

Your guests, made up of: Jared, Gen, Abby, Daneel, her husband; Mike, Justice, Arrow, Zeppelin, Alan, Donna, and a small splattering of other close family members and friends of both yours and Jensen’s began chanting, “Kiss her! Kiss her! Kiss her!” 

You cheeks turned a deep crimson as Jensen grabbed your waist and dipped you before kissing you. The crowd erupted in laughter and cheers. 

As Jensen helped you stand back up, the DJ voice filtered through speakers set up around the patio, “Okay guys. It’s time for the couple’s first dance. They’re dedicating this dance to Y/N’s late parents, dancing to their first dance song, Stand by Me.” 

As you and Jensen came together, moving slowly to the rhythm of the music, tears started to fall down your face slowly as you danced. Jensen brushed a tear away before kissing your forehead and pulling you closer to him. You swayed in a tight embrace as the loss of your parents hit you hard. 

It was the worst, not having them finally see you be happy and experience this day with you. But you knew they were here, in some way, watching over you. 

Jensen whispered into your ear as you both continued to dance, “I love you, Mrs. Y/N Ackles.” 

“And I love you, Mr. Jensen Ackles.”


End file.
